14252-05-2Relevant academic research and scientific papers
Bicyclo[3.2.1]octanes: Synthesis and inhibition of binding at the dopamine and serotonin transporters
Meltzer, Peter C.,Blundell, Paul,Chen, Zhengming,Yong, Yaw F.,Madras, Bertha K.
, p. 857 - 862 (1999)
Herein we report the synthesis of a series of bicyclo[3.2.1]octanes and their binding characteristics at the dopamine and serotonin transporters. The data confirm that a heteroatom at position 8 of the tropane nucleus is not a prerequisite for binding since the bicyclo[3.2.1]octanes prove potent inhibitors of both transporters. Therefore the three-dimensional topology of the ligand may be more important than specific functionality with respect to stereospecific binding at the acceptor site.
Polycyclo Dyes and Use Thereof
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Paragraph 0152, (2013/06/05)
The invention relates to a family of fluorescent compounds that comprise a bridged polycyclo moiety. The compounds can be chemically linked to biomolecules, such as proteins, nucleic acids, and therapeutic small molecules. The compounds can be used for imaging in a variety of medical, biological and diagnostic applications, and are particularly useful for the in vivo imaging of regions of interest within a mammal.
COMPOUNDS AND METHODS FOR THE TREATMENT OR PREVENTION OF FLAVIVIRUS INFECTIONS
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Page/Page column 147, (2008/06/13)
Compounds represented by formula (I) : or pharmaceutically acceptable salts and solvates thereof, wherein R1, X, Y, Y1, and Z are as defined herein, are useful for treating flavivi?dae viral infections Said viral infection is Hepatitis C virus (HCV), bovme viral diarrhea virus (BVDV), hog cholera virus, dengue fever virus, Japanese encephalitis virus or yellow fever virus
Structure activity relationships of inhibition of the dopamine transporter by 3-arylbicyclo[3.2.1]octanes
Meltzer, Peter C.,Blundell, Paul,Madras, Bertha K.
, p. 12 - 34 (2007/10/03)
In this report we present an overview of the Structure Activity Relationships (SAR) which govern the interaction of 3- arylbicyclo[3.2.1]octanes (tropane analogs) with the dopamine transporter (DAT). Data for inhibition of the DAT by bicyclo[3.2.1]octanes modified at C- 2, C-3, C-7 and 8-N are presented and discussed. We postulate that the three dimensional volume of the bicyclo[3.2.1]octanes influences binding to the DAT and may play a greater role in inhibition of the transporter than does the presence of specific functionality.
Ring expansions of 2-haloethynyl-2-norbornanols
Djuardi, Elsa,Bovonsombat, Pakorn,Mc Nelis, Edward
, p. 11793 - 11802 (2007/10/02)
2-Haloethynyl-2-norbornanols react with iodine and Koser's reagent in acetonitrile to afford two ring-expanded products, 2-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-3-one and 3-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-2-one. These results contrast with the 2-haloethynyl-2-bornanols which lead to the corresponding 3-octanones.
Novel photoactive compounds, processes for their production and intermediates therefor
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, (2008/06/13)
Photoactive compounds having the general formulae below are provided in which A represents oxygen or specified imido groups;, P1 represents a 3-furyl, a 3-thienyl, a 3-pyrryl, a 3-benzofuryl or a 3-benzothienyl group, said 3-furyl, 3-thienyl and 3-pyrryl groups which is unsubstituted or substituted in the 2-position and/or the 5-position, with specified substituents;, P2 represents alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aralkyl having 7 to 9 carbon atoms, aryl having 6 to 14 carbon atoms which may be unsubstituted or substituted with one or more halogen atoms, or alkaryl having 7 to 22 carbon atoms; and,
Ring Expansion of Ketones to 1,2-Keto Thioketals. Control of Bond Migration
Knapp, Spencer,Trope, Adrea F.,Theodore, Michael S.,Hirata, Naonori,Barchi, Joseph J.
, p. 608 - 614 (2007/10/02)
A practical two-step procedure for the title transformation has been developed.Treatment of cyclic ketones with (CH3S)3CLi gave adducts 6 and 13-17, which underwent ring expansion at 75 deg C in the presence of CuBF4*4CH3CN to the keto thioketals 7 and 18-21.In the cases examined the reaction was highly regioselective, giving the product resulting from migration of the more substituted carbon.The procedure has been used to prepare a key bicyclic intermediate (33) for a total synthesis of (+/-)-coriolin (1).An alternative synthesis of 33 suggests that were there is steric crowding in the vicinity of the tris(methylthio)methyl group of the adduct, the bond migration is controlled by the location of the obtruding group.
DEAMINATION OF ENDO - AND EXO-BICYCLOOCTAN-3-YLAMINES AND THEIR DERIVATIVES
Maskill, H.,Wilson, Alan A.
, p. 1369 - 1376 (2007/10/02)
Bicyclooctan-3-ylamines have been deaminated in acetic acid by nitrous acid and via their N-phenyltriazines; their ethyl N-nitrosocarbabamates have also been solvolysed in ethanol.The exo-isomers give mainly unrearranged substitution, some elimination, and very little rearrangement.The unrearranged substitution is derived from both the solvent (the external nucleophile, either acetic acid or ethanol) and internal nucleophile liberated in the deaminative fragmentation step (water from the nitrous acid reaction, aniline from the triazene, and ethyl carbonate from the nitrosocarbamate).It is of predominantly retained configuration i n all three reactions with the solvents, and, as demonstrated in the solvolysis, with the internal nucleophile.The endo-isomers give mainly elimination, some unrearranged substitution, and appereciable rearrangement.The solvent-derived unrearranged substitution is with predominant inversion of configuration in all three reactions whereas that from the internal nucleophile, established by the nitrosocarbamate solvolysis, is predominantly with retention.Rearangement from both endo- and exo-compounds is best explained in terms of hydride shift from the first formed carbonium ions (in nitrogen-separated complex ion-pairs with hydrogen-bonded anions) produced in the deaminative fragmentation.This gives rearranged classical bicyclooctan-2-yl carbonium ions which, in competition with nucleophilic capture and proton loss, undergo further stepwise rearrangement to a common unsymmetrical non-classical carbonium ion.The non-classical cation and its classical precursors (which, from exo-and endo-substrates, differ in the location of the counter-anion) give rise to substitution products derived from solvent and the internal nucleophile.The non-classical carbonium ion also gives some tricyclo2,7>octane.The high yields of internal substitution products from both endo- and exo-compounds rule out long lived intermediates such as diazonium ions.
RING EXPANSION OF KETONES TO 1,2-KETO-THIOKETALS
Knapp, Spencer,Trope, Adrea F.,Ornaf, Raphael M.
, p. 4301 - 4304 (2007/10/02)
Treatment of cyclic ketones with (MeS)3C-Li, then CuClO4.4CH3CN, gives the corresponding ring expanded 1,2-keto-thioketals.
